Solid diazoazometal halide dottble salt



Patented Nov. 29, 1932 UNITED STATES PA N o cs mini. 'sczrnirzsmnn ororrnmsAcir-on-rnE-mm,GERMANY, Assrenon T GEN- nan. ANILINE worms, me, or nnw vonn, 1v. =Y., A CORPORATION 01' DELAWARE- soiirn nmaonzomn 'ru. HALI'DE'DOUBLE SALT 7 No sawing. Application fl1edSepte mber 29; 1927, Serial No. 222,943, and in Germany October 5,1926.

invention relates to solid diazoazo me tallic halide double salts correspond ng prob.- ably to the general formula:

pounds not containing a sulfonic. or carboxylic group and aminoderivatives of monoor polyvalent aryloxyalkylethers,such as orthoaminophenolether, aminocresolet'her, aminohydroquinoneiethers, 1.2 aminonaphthol ethers and derivatives capable offormlng para-aminoazobodies, and separating the d1- azosalts in form ofmetallic double salts by adding a" metallic halide salt and-preferably an alkali metal halide salt, such as common salt to the di azo solutions. As such metallic halide salts those of heavy metals, such as zinc chloride orstannic chloride, mercury,

auricandplatinic chloride may be na ed;

washitherto unknown that the monodiazoazocompounds of the aforesaid chemical constitution can be isolated in a solid form and that the stability of the solid products is sufficient for the use for dyeing and printingpurposes, and only the corresponding diazo solutions new made from. the bases .were used hitherto, for" instance, for the process of U. S. A. Patent No. 1398, 117 Therefore, the present solid diaz o'azocompounds are new products, they are orangeto reddish brown colored powders soluble in water with ayellowish to reddishbrown color, they surpass the "hitherto isolated solid .diazocompounds of other 'aminoazocompounds not containing the typical lalkoxygroup, for instance, those described German Patent 89,437, in their properties, es- ..pecially by their good solubility and, their exc l Stab l y:

,it maybe mixed with a suitable'diluent be- "foreor after being dried. It represents an The stability and the commercial value of thenew .solid diazoazocompounds is appar and other suitable diluents, theymay be used for producing azo-dyestuffs on the fiber and allow to supply the userwith diazoazoconn pounds yielding particularly valuable disazodyestuifs in a most concentrated form imme diately ready for the use. r In order to further illustrate my invention the following examples are given, the parts being by weight andall temperatures in centigrade degrees, but it is understood that my invention is not limited to the particular products or reactingconditions mentioned therein; Y Ewample 1.-A-diazosolution obtained by diazotizing in dilute hydrochoric "acid 272 parts of the para-amino-azo-body derived from diazotized meta-nitrdaniline and ortho-anisidine is precipitated by adding, for instance, parts of zinc chloride and*1000 parts of common salt. The zinc chloride doublel'sa'lt corresponding probably to the formu a: L

orange-brown powder, soluble in a brownish color;

Ewample a-A amass chloride S0111- water with tion obtained from 302 parts of th-e paraamino-azo-body: para-n-itrobenzene-azo 2 amino-1A-dimethoxybenzene is precipitated with 100 parts of zinc chloride and a suflicient amount of common salt. The zinc chloride double salt thus obtained corresponding probably to the formula:

OCH

roaiiiline and 1'-"a mino-2ethoxynaphthalene,

is treated as described inthe foregoing example, The diazosalt obtained "corresponds probably tothe formula: V r

coin.

It foims'a brownish powder, soluble in water with a: brownish color.

In the same manner the dia'zosalts-of the aminoazobodies derived from diazotized 1 and 2-naphthylamine' and 4-nitro-1-naphthylar'nine and from aminohydroquinone-dimethylether may be separated in solid form.

,Ew'ample 4.A diazoniumchloride solution, obtained from 276 parts of the :paraaminoazobody orthochlorobenzeneazo 3 amino l-methoxy-l-methylbenzene is precipitated with abfout"150 parts of stannicchloride and a little quantityof common salt. Thefdouble' salt thus separating corresponds probablyto theformula: I i 'CH| I v V v V QM c1 OCH: 2 I: 7

It is filtered and "dried. It represents a brownish'powder.

Ewa-mple 5.-A di azonium chloride solution obtained from the aminoazobody :Q-me thoxybenzene-azo 2-amino 1.4 dimethoxy benzene is treated as described in the foregoing example. The double salt thus separating corresponds probably to the formula: v

OCH;

in is 'filtere'd addried. it re resents brownishjpow-der. ,7

:E'wample 6',- ,A diazonium chloride solu- "tion obtained from 300 parts of thea'ininoazobody para-nitro-benzene-azo-3amino-4- methoxy 1 methylbenzene is precipitated with, for instance, 7 5 parts of zinc chloride and common salt. The zinc chloride double salt, thus separating in crystalline form, corresponds probably to the formula:

, It -is filtered and dried.

In the same manner the aminoazobodies, derived from diazotized 4- and 5-nitro-2- amino-l-anisol, land Q-naphthylamine and 4-nitro-1-napthylamine and from pjara-cr'esidine may be converted into solid salts.

I claim: 1

1. Solid diazoazo metallic halide double salts corresponding probably to the general formulaz- (O-zilkjlh R1--N=NR v I .M8(l18l089l1)z+l 2 wherein Rand R mean aryl 'radicals'not containing as'ulfonic or carboxylic acid :group, "n stands for a number being at least 1, and

w for a number-correspon'ding'to the valence of the metal signified by Me, which solid dia'zo'azo double-salts are orange to reddish- 'brown powders, soluble in water with a yellowish to reddis'h browncolor. V V

' 2. Solid *diazoazo metallic halide double salts corresponding probably to the general formu'l'az' wherein R andR -mean'aryl radicals not containing-a sulfonic or carboxylic acid group,

n stands for a number being at least 1,'a'nd i m m for a number corresponding to the valence of the metal signified by Me, and wherein one -Q-alkyl gr0up stands in or'tho-position to the diazonium group, which solid diazoazo .double salts are orange to reddish-brown vvpowders,soluble in water with a yellowish 'to reddish brown color. V r y Y '3. Solid dia z oazo metallicchloride double salts corresponding probably to the general wherein Rand R m'ean aryl radicals'not'con- 'tai'ning a sulfonic or *carb'o'xylic acid group, 'n stands fora number being "at least "1, Me f 's'tands for a metal-ofthe"groupconsistingof Zn and Sn, and" a: for 'a number corresponding to the valance of the metal, and wherein isa one -O-alkyl group stands in ortho-position to the diazonium group, which solid diazoazo double salts are orange to reddish brown powders, soluble in water with a yellowish to reddish-brown color.

4. Solid diazoazo zinc chloride double salt corresponding probably to the formula:

OOH:

which solid diazoazo zinc chloride double salt is a reddish-brown powder, soluble in water with a brownish color. 7

5. Solid diazoazo zinc chloride double salt correspondingprobably to the formula:

which solid diazoazo zinc chloride double salt is a brownish powder, soluble in water with a brownish color. 7

6. Solid diazoazo stannic chloride double salt corresponding probably to the formula:

which solid diazoazo stannic chloride double salt is a brownish powder.

In testimony whereof, I affix my signature.

KARL SCI-INITZSPAHN. 

